The Entrepreneur's Journey

Article Published: May 15, 2015

Share on:

The Entrepreneur’s Journey

Difficult things come at great cost, and entrepreneurs do the most difficult of things at a cost paid in more than dollars. No customers, no prospects, growing piles of debt, disappointed investors, discouraged colleagues, fractured personal relationships, and yet the entrepreneur presses forward. Even close friends and family see no point in going on. “My boyfriend woke up at 3 AM to find me sitting in a chair looking out the window,” recalled one entrepreneur. “He said ‘Honey, this is killing you’ and he wasn’t far from the truth,” while she pointedly added, “but something in me just would not let me quit.”

When passing through the hardest of hard times, there is a terrible pressure from within and without to give up. Yet, to paraphrase Oscar Wilde, “[Entrepreneurs] see the donut, [everyone else] sees the hole.” A friend relates, “I never know when to pack it up and move on. Just when things are not going well at all, some good unexpected thing comes along and I’m suddenly like ‘OK, let’s give it another go and see what happens’,” he added.

I must admit up front that at times I wanted to quit my entrepreneurial journey, the reasons for which I’ve thankfully forgotten. But I did not and I’m glad I did not. I wrote this piece to share the emotions I experienced and difficult dilemmas I faced along the way. My journey is far from over but this article is a reminder to me of what it took to get to here and what I need to remember to keep pushing further. So if you’re working at your dream and now find yourself, for whatever sound reason, considering quitting, please read on.

There is no handy business logic, spreadsheet or analytic model to tell you when to make a prudent business decision to pack it in. This may be because starting a business isn’t a prudent business decision in the first place. In fact, it is a personal one defying good common sense.

In my case, we founded kWantera (under a different company name) to help Soldiers, SEALs and Marines “see” the dangers lurking around corners and behind walls. Yet all our efforts to convince the military our throwable sensing devices could do just that were, for different reasons, for naught—though not for lack of effort and money. To say we were disappointed is understatement in the extreme.

When things go south, you can’t help but think about all the now obvious missed opportunities and mistakes you and your colleagues made along the way that put you in this terrible mess. Why did we hire that guy? I knew we were spending too much money and spending it too fast. We were building stuff no one wanted. True as these things may be, they as we shall see, miss the point.

I recall an astonishing exchange I had at a military trade show some years ago with a wildly successful and well-known entrepreneur whose tools of war are used by all US service branches and militaries around the world. “I was more or less functionally broke for about 18 years, Mark, building my business,” he eagerly shared. He continued, “Almost everyone we spoke to said there is just no real need for [our product]. The Marines said it was too big and the Army said there was little practical need for it. But I pretty much kept ignoring the people who poo-poo’d us or who said no and paid close attention to the people that thought like me.”

I like biographies of individuals who overcame long or (better) impossible odds. I’m also always eager to hear how my fellow entrepreneurs deal or dealt with truly hard times. From all that I learned one simple and obvious truth: persistence really works. Mind you, not just some persistence, but a whole hell of lot.

But the fact is it is sometimes hard to tell the difference between persistence and mad obsession. There is no bright line between the two. This is scary and may be one reason some people find the idea of being an entrepreneur unappealing. Not for a fear of failure, but rather a fear of not being able to fulfill the total, open-ended, emotional and psychological commitment necessary to pursue your most cherished dreams; I protect myself from heartbreak by never giving my whole heart.

Yet the hard but beautiful truth is that during the toughest of times—when pressing on is impossible to rationally justify—is the moment when human will and heart is most precious and exquisitely felt by the entrepreneur and visible to the world.

The tools we take for granted in our everyday lives, like cellphones, cars and the Internet, were hardly considered possible just before or even as they were coming into being. In fact, the amazing things countless entrepreneurs brought into being fought with the incredibly powerful forces of inertia, entrenched powers and established routines. Machiavelli observed half a millennium ago, ‘…There is nothing more difficult to take in hand, more perilous to conduct, or more uncertain in its success, than to take the lead in the introduction of a new order of things.’

Many a smart consultant, executive and professor did not believe 30 years ago that every person on the planet would soon have a cell phone. Nor did leading thinkers in the entertainment industry predict 20 years ago we would all be purchasing our music online very soon. Who among us could have seen even a few years ago that someone somewhere would build a global $40B Internet-based taxi service in just a few years?

After my colleagues and I picked ourselves off the ground from our failed effort to sell hardware to the US military, we ‘pivoted’ to energy. Our change of direction was opportunistic, but it was still yet another theory of what we believed we could do well. Nevertheless, we took the new plunge with a lot of new theories followed by a lot of new experimentation. To our pleasant surprise, we found that the problems of real-time prediction in electricity and natural gas markets were not that different from the problems of real-time analysis we creatively addressed on behalf of the US military.

The core psychic energy source for our about-face pivot was a survival instinct born of a basic unwillingness by the people in our fledgling company to give up even though quitting would probably have been both a prudent personal and business decision at the time.

Herein is a dilemma. Psychologically, emotionally and physically brutal contests with an uncertain end and high probability of failure can break the strongest of us. Panic and fear take hold. In his book The Hard Thing About Hard Things, entrepreneur and venture capitalist Ben Horowitz believes, “Hard things are hard because there are no easy answers or recipes. They are hard because your emotions are at odds with your logic. They are hard because you don’t know the answer and you cannot ask for help without showing weakness.”

Boot camps are designed with the express purpose of pushing young men and women to the limits of their endurance and finding their limits and then slowly and carefully bringing them back to make a confident soldier or Marine. Entrepreneurs experience something similar, but their boot camps only end when: (1) the business fails, (2) the entrepreneur quits, (3) the entrepreneur is thrown out or (4) the company is acquired. The first three of these alternatives are terribly painful and yet they’re the most probable outcome.

Who or what protects the entrepreneur? My experience is the recognition that you are not alone. Yet therein is another difficult dilemma.

The decision to stay at the wheel of fortune and keep spinning is the entrepreneur’s alone, but the consequences of it are not. And by refusing to quit you pull, push and prod family, employees, friends, partners, customers and investors to stay at it with you. Is it ethical to ask them to take this headlong charge into the darkness again and again (and again) with me? What if I’m wrong, misguided or perhaps even delusional? I’m asking them to put their savings, careers, reputations—their heart and soul—into something that I sometimes, in my darkest moments, question.

This particular dilemma is tethered to another challenge entrepreneurs face, which is the ever-present feeling of “aloneness.” Not loneliness, though that too is sometimes a reality. As a cofounder, you were the one who stimulated the initial commitment of time and money from friends and colleagues. As you progress, strangers join you on this journey, and somewhere along the way you feel the burden that all of this commitment exists because you’ve convinced them to join you. If it fails it is on you, you believe. It is this self-perception (but not the fact) that you’re ultimately alone, despite the most supportive of family, friends and cofounders.

There are internal and imaginary conversations that play out in minds of entrepreneurs that bring deep doubts, fears and even moments of stark terror. Such is the lot of the man or woman who gets up every morning to try to change the status quo in a large and remarkable way.

Yet perhaps the most difficult of dilemmas entrepreneurs contend with is the constant, unrelenting burden of making impossible choices. The vice and the virtue of working in a large organization a friend once told me, is that most of the time nothing much happens, so no decisions get or need to be made. That is not true for startups, as they’re at the same time agile and fragile. Damn difficult choices must be made almost daily, whether the entrepreneur wants to or not, the effects of which will be felt in an indefinite and uncertain future.

That does not mean entrepreneurs should not adapt as circumstances require—to ‘pivot.’ But there is a big difference between pivoting in order to continue to pursue your dream and pivoting for the sake of pivoting. There is a subtle but important difference between the two ways of adapting.

Pivoting for the sake of pivoting calls into question the very motivation of creating the company in the first place. Pivoting to pursue the dream from a different point of attack is entirely a different matter. We believed that our way of looking at the world through real-time public data was capable of making an important difference in a person’s daily life. Our original means of realizing that vision was by helping our nation’s service men and women in time of war. That path was not feasible, but we were fortunate to find another by helping people buy, sell and consume energy more efficiently and effectively.

But it is the fact of the hardship, setbacks, and sacrifices that—strange as it sounds—motivates some to put everything they care about on the line for something greater. I do not know a single entrepreneur who would trade all the fear, uncertainty and raw personal pain they endured to build and sometimes rebuild something from nothing.

However, the challenge every entrepreneur faces is not to avoid pain or learn to grudgingly accept it. It is to embrace the pain, fear and ocassional terror as a constant reminder that, though you’re doing a hard thing, you’re also likely doing the right thing.

“When you’re frozen with fear like I was, you can’t do your job,” my father said to me in an unfamiliar tone late one summer night a long time ago. He added, “Once I knew, not thought but knew, I would die right there on that beach I could start doing it,” which for him was risking his own life to save others in the middle of a long and brutal battle in WWII.

I remember this moment for many reasons, but two always come to mind. First, my father never, ever talked about his experiences as a Navy Corpsman on Iwo Jima. Second, it reminds me what is necessary to do a very difficult but very worthy thing: total, unflinching commitment in the face of near certain defeat. Those precious few worthy goals in life that demand our heart and soul never happen how, where and when we want them to, but they do not happen at all if we quit.

We ultimately found some great partners and the needed capital to take our business to a new level. There is so much more to do and learn, which invigorates me even more. For example, even though my title remains the same, my role has changed substantially. But, you will be hearing more about that along all the other challenges I’ve faced and now face along the way.